US6824811B2 - Concentrate of triterpenes - Google Patents
Concentrate of triterpenes Download PDFInfo
- Publication number
- US6824811B2 US6824811B2 US10/118,319 US11831902A US6824811B2 US 6824811 B2 US6824811 B2 US 6824811B2 US 11831902 A US11831902 A US 11831902A US 6824811 B2 US6824811 B2 US 6824811B2
- Authority
- US
- United States
- Prior art keywords
- acid
- concentrate
- amount
- oleanoic
- ursolic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related, expires
Links
- 239000012141 concentrate Substances 0.000 title claims abstract description 35
- 150000003648 triterpenes Chemical class 0.000 title claims abstract description 7
- WCGUUGGRBIKTOS-GPOJBZKASA-N (3beta)-3-hydroxyurs-12-en-28-oic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C WCGUUGGRBIKTOS-GPOJBZKASA-N 0.000 claims abstract description 31
- 229940096998 ursolic acid Drugs 0.000 claims abstract description 31
- PLSAJKYPRJGMHO-UHFFFAOYSA-N ursolic acid Natural products CC1CCC2(CCC3(C)C(C=CC4C5(C)CCC(O)C(C)(C)C5CCC34C)C2C1C)C(=O)O PLSAJKYPRJGMHO-UHFFFAOYSA-N 0.000 claims abstract description 31
- MIJYXULNPSFWEK-LGSDIRQTSA-N (4as,6as,6br,10r,12ar)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid Chemical compound C1C[C@@H](O)C(C)(C)C2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)CC5C4=CCC3[C@]21C MIJYXULNPSFWEK-LGSDIRQTSA-N 0.000 claims abstract description 29
- FMIMFCRXYXVFTA-UHFFFAOYSA-N 3-Oxo-12-oleanen-28-oic acid Natural products C1CC(=O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4=CCC3C21C FMIMFCRXYXVFTA-UHFFFAOYSA-N 0.000 claims abstract description 29
- MIJYXULNPSFWEK-UHFFFAOYSA-N Oleanolinsaeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4=CCC3C21C MIJYXULNPSFWEK-UHFFFAOYSA-N 0.000 claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 29
- MXEMKMNFLXVQBW-UHFFFAOYSA-N oleanoic acid Natural products C1CCC(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4=CCC3C21C MXEMKMNFLXVQBW-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000000463 material Substances 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 235000000346 sugar Nutrition 0.000 claims abstract description 13
- 125000005456 glyceride group Chemical group 0.000 claims abstract description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 40
- 235000013305 food Nutrition 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 14
- 238000001035 drying Methods 0.000 claims description 14
- 238000003801 milling Methods 0.000 claims description 12
- 239000005445 natural material Substances 0.000 claims description 12
- 239000000047 product Substances 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000002245 particle Substances 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 7
- 238000000227 grinding Methods 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 6
- 150000008163 sugars Chemical class 0.000 claims description 6
- 235000015872 dietary supplement Nutrition 0.000 claims description 5
- 239000003929 acidic solution Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 238000011282 treatment Methods 0.000 claims description 4
- 235000021016 apples Nutrition 0.000 claims description 3
- 230000037396 body weight Effects 0.000 claims description 3
- HQZKQSIAHGHXDL-UHFFFAOYSA-N 2-oxo-pomolic acid Natural products C1C(=O)C(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)C(O)(C)C5C4=CCC3C21C HQZKQSIAHGHXDL-UHFFFAOYSA-N 0.000 claims description 2
- 108010010803 Gelatin Proteins 0.000 claims description 2
- 229920000881 Modified starch Polymers 0.000 claims description 2
- ZZTYPLSBNNGEIS-OPAXANQDSA-N Pomolic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@](O)(C)[C@H]5C4=CC[C@@H]3[C@]21C ZZTYPLSBNNGEIS-OPAXANQDSA-N 0.000 claims description 2
- JYEJQUHSBMDABO-SYKQLJDKSA-N Pomolic acid Natural products C[C@@H]1CC[C@@]2(CC[C@H]3[C@@H]4CC[C@H]5C(C)(C)[C@@H](O)CC[C@]5(C)[C@H]4CC=C3[C@@H]2[C@]1(C)O)C(=O)O JYEJQUHSBMDABO-SYKQLJDKSA-N 0.000 claims description 2
- 229920002472 Starch Polymers 0.000 claims description 2
- 229920000159 gelatin Polymers 0.000 claims description 2
- 239000008273 gelatin Substances 0.000 claims description 2
- 235000019322 gelatine Nutrition 0.000 claims description 2
- 235000011852 gelatine desserts Nutrition 0.000 claims description 2
- 239000000416 hydrocolloid Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- MDZKJHQSJHYOHJ-LLICELPBSA-N maslinic acid Chemical class C1[C@@H](O)[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C MDZKJHQSJHYOHJ-LLICELPBSA-N 0.000 claims description 2
- 235000019426 modified starch Nutrition 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims description 2
- 235000019698 starch Nutrition 0.000 claims description 2
- 150000003505 terpenes Chemical class 0.000 claims description 2
- 235000007586 terpenes Nutrition 0.000 claims description 2
- 244000141359 Malus pumila Species 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 20
- 241000220225 Malus Species 0.000 description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 11
- 235000011007 phosphoric acid Nutrition 0.000 description 10
- 235000017550 sodium carbonate Nutrition 0.000 description 10
- 229910000029 sodium carbonate Inorganic materials 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000000605 extraction Methods 0.000 description 7
- 239000013049 sediment Substances 0.000 description 7
- 239000012467 final product Substances 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 239000002585 base Substances 0.000 description 4
- 235000013399 edible fruits Nutrition 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000009482 thermal adhesion granulation Methods 0.000 description 3
- -1 triterpene acids Chemical class 0.000 description 3
- 238000003811 acetone extraction Methods 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 235000014633 carbohydrates Nutrition 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000769 gas chromatography-flame ionisation detection Methods 0.000 description 2
- 238000002203 pretreatment Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 229930091371 Fructose Natural products 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- XCOBLONWWXQEBS-KPKJPENVSA-N N,O-bis(trimethylsilyl)trifluoroacetamide Chemical compound C[Si](C)(C)O\C(C(F)(F)F)=N\[Si](C)(C)C XCOBLONWWXQEBS-KPKJPENVSA-N 0.000 description 1
- 241001307210 Pene Species 0.000 description 1
- 241001479493 Sousa Species 0.000 description 1
- 238000000944 Soxhlet extraction Methods 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000010420 art technique Methods 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- MDZKJHQSJHYOHJ-UHFFFAOYSA-N crataegolic acid Natural products C1C(O)C(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4=CCC3C21C MDZKJHQSJHYOHJ-UHFFFAOYSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
- A23D9/007—Other edible oils or fats, e.g. shortenings or cooking oils characterised by ingredients other than fatty acid triglycerides
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/03—Organic compounds
- A23L29/035—Organic compounds containing oxygen as heteroatom
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Nutrition Science (AREA)
- Botany (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Mycology (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Obesity (AREA)
- Veterinary Medicine (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Cosmetics (AREA)
- Medicines Containing Plant Substances (AREA)
- Extraction Or Liquid Replacement (AREA)
- General Preparation And Processing Of Foods (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01201296 | 2001-04-09 | ||
| EP01201296 | 2001-04-09 | ||
| EP01201296.9 | 2001-04-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| US20030049365A1 US20030049365A1 (en) | 2003-03-13 |
| US6824811B2 true US6824811B2 (en) | 2004-11-30 |
Family
ID=8180120
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US10/118,319 Expired - Fee Related US6824811B2 (en) | 2001-04-09 | 2002-04-09 | Concentrate of triterpenes |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US6824811B2 (enExample) |
| JP (1) | JP2002345434A (enExample) |
| CN (1) | CN100448887C (enExample) |
| AT (1) | ATE295087T1 (enExample) |
| DE (1) | DE60204078T2 (enExample) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100715309B1 (ko) | 2005-05-17 | 2007-05-04 | 한국콜마 주식회사 | 해리상수를 이용하여 용해된 우르솔산과 제미니형계면활성제를 함유하는 피부주름개선 화장료 및 이의제조방법 |
| US20100204121A1 (en) * | 2009-02-10 | 2010-08-12 | Romero Augustin T | Dietary supplements containing terpenoid acids of maslinic acid or oleanolic acid and process for enhancing muscle mass in mammals |
| WO2019055245A1 (en) | 2017-09-14 | 2019-03-21 | Phoenix Biotechnology, Inc. | IMPROVED METHOD AND COMPOSITION FOR THE TREATMENT OF TRITERPENE SENSITIVE CONDITIONS, DISEASES OR DISORDERS |
| WO2019055119A1 (en) | 2017-09-14 | 2019-03-21 | Phoenix Biotechnology, Inc. | METHOD AND COMPOSITION FOR TREATING VIRAL INFECTION |
| WO2021201903A1 (en) | 2020-03-31 | 2021-10-07 | Phoenix Biotechnology, Inc. | Method and compositions for treating coronavirus infection |
| EP4295854A2 (en) | 2020-03-31 | 2023-12-27 | Phoenix Biotechnology, Inc. | Method and compositions for treating coronavirus infection |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007514727A (ja) * | 2003-12-19 | 2007-06-07 | リピッド ニュートリション ベスローテン フェンノートシャップ | 過敏症および過反応症の治療用医薬の調製のためのオレアノール酸およびウルソル酸を含む組成物の使用 |
| JP2008255085A (ja) | 2007-04-04 | 2008-10-23 | Tokiwa Shokubutsu Kagaku Kenkyusho:Kk | 枇杷葉からの高純度コロソリン酸及び高純度ウルソール酸の製造方法 |
| KR101393438B1 (ko) * | 2012-10-05 | 2014-05-12 | 경상북도(농업기술원) | 사과껍질로부터 우르솔릭산을 추출하는 방법 |
| JP2015189691A (ja) * | 2014-03-27 | 2015-11-02 | 公益財団法人東洋食品研究所 | Ｇｐｄｈ活性抑制剤 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1152221B (de) | 1954-07-20 | 1963-08-01 | Elisabeth Ullsperger Geb Dotza | Verfahren zur Gewinnung von Triterpensaeuren |
| FR2541895A1 (fr) | 1983-03-04 | 1984-09-07 | Jean Daniel | Composition deodorante et antitranspirante a base d'acide triterpenique |
| EP0555484A1 (en) | 1990-11-21 | 1993-08-18 | Hokkaidosugar Co., Ltd. | Water-soluble pentacyclic triterpene composition and production thereof |
| US5948460A (en) | 1998-07-27 | 1999-09-07 | Takasago International Corporation | Flavored product additive and method for using same |
| US6123968A (en) * | 1999-03-23 | 2000-09-26 | Mendez; Alejandro | Composition for extending shelf life for fresh fruits and vegetables without the use of refrigeration |
| US20020019253A1 (en) * | 1997-05-05 | 2002-02-14 | Robert Reitzen | Computer gaming system |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1045585A (zh) * | 1990-04-03 | 1990-09-26 | 邵雅旭 | 一种从植物中提取齐墩果酸的方法 |
-
2002
- 2002-03-13 DE DE60204078T patent/DE60204078T2/de not_active Expired - Lifetime
- 2002-03-13 AT AT02075966T patent/ATE295087T1/de not_active IP Right Cessation
- 2002-04-09 JP JP2002106253A patent/JP2002345434A/ja active Pending
- 2002-04-09 US US10/118,319 patent/US6824811B2/en not_active Expired - Fee Related
- 2002-04-09 CN CNB021060282A patent/CN100448887C/zh not_active Expired - Fee Related
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1152221B (de) | 1954-07-20 | 1963-08-01 | Elisabeth Ullsperger Geb Dotza | Verfahren zur Gewinnung von Triterpensaeuren |
| FR2541895A1 (fr) | 1983-03-04 | 1984-09-07 | Jean Daniel | Composition deodorante et antitranspirante a base d'acide triterpenique |
| EP0555484A1 (en) | 1990-11-21 | 1993-08-18 | Hokkaidosugar Co., Ltd. | Water-soluble pentacyclic triterpene composition and production thereof |
| US20020019253A1 (en) * | 1997-05-05 | 2002-02-14 | Robert Reitzen | Computer gaming system |
| US5948460A (en) | 1998-07-27 | 1999-09-07 | Takasago International Corporation | Flavored product additive and method for using same |
| US6123968A (en) * | 1999-03-23 | 2000-09-26 | Mendez; Alejandro | Composition for extending shelf life for fresh fruits and vegetables without the use of refrigeration |
Non-Patent Citations (1)
| Title |
|---|
| Bock et al, "Bestandteile der aus Appeltrockentrestern Gewinnbaren Triterpenfraktion", Die Nahrung, VCH Verlagsgesellschaft, Weinheim, vol. 10, No. 5, 1966, pp. 409-412. |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100715309B1 (ko) | 2005-05-17 | 2007-05-04 | 한국콜마 주식회사 | 해리상수를 이용하여 용해된 우르솔산과 제미니형계면활성제를 함유하는 피부주름개선 화장료 및 이의제조방법 |
| US20100204121A1 (en) * | 2009-02-10 | 2010-08-12 | Romero Augustin T | Dietary supplements containing terpenoid acids of maslinic acid or oleanolic acid and process for enhancing muscle mass in mammals |
| US8822536B2 (en) | 2009-02-10 | 2014-09-02 | Fhg Corporation | Dietary supplements containing terpenoid acids of maslinic acid or oleanolic acid and process for enhancing muscle mass in mammals |
| WO2019055245A1 (en) | 2017-09-14 | 2019-03-21 | Phoenix Biotechnology, Inc. | IMPROVED METHOD AND COMPOSITION FOR THE TREATMENT OF TRITERPENE SENSITIVE CONDITIONS, DISEASES OR DISORDERS |
| WO2019055119A1 (en) | 2017-09-14 | 2019-03-21 | Phoenix Biotechnology, Inc. | METHOD AND COMPOSITION FOR TREATING VIRAL INFECTION |
| WO2021201903A1 (en) | 2020-03-31 | 2021-10-07 | Phoenix Biotechnology, Inc. | Method and compositions for treating coronavirus infection |
| EP4295854A2 (en) | 2020-03-31 | 2023-12-27 | Phoenix Biotechnology, Inc. | Method and compositions for treating coronavirus infection |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1380302A (zh) | 2002-11-20 |
| CN100448887C (zh) | 2009-01-07 |
| US20030049365A1 (en) | 2003-03-13 |
| JP2002345434A (ja) | 2002-12-03 |
| ATE295087T1 (de) | 2005-05-15 |
| DE60204078T2 (de) | 2006-01-26 |
| DE60204078D1 (de) | 2005-06-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Piga | Cactus pear: a fruit of nutraceutical and functional importance | |
| Hwang | Sesame oil | |
| JP4428740B2 (ja) | ビフィズス菌増殖促進剤 | |
| US6824811B2 (en) | Concentrate of triterpenes | |
| RU2466736C2 (ru) | Экстракт из растительного сырья с высоким содержанием полифенола | |
| KR101220135B1 (ko) | 항산화기능을 갖는 블루베리 음료 프리믹스 조성물의 제조방법 | |
| PL203697B1 (pl) | Sposób wytwarzania pełnego ekstraktu pomidorowego | |
| He et al. | Phytochemicals, nutritionals and antioxidant properties of miracle fruit Synsepalum dulcificum | |
| JPWO2010092941A1 (ja) | 血管拡張作用を有する組成物、製造法および用途 | |
| Pandey et al. | Characterization of black carrot (Daucus carota L.) polyphenols; role in health promotion and disease prevention: An overview | |
| JP4358957B2 (ja) | フリーラジカル又は活性酸素を消去もしくは低減する剤 | |
| CN114766683A (zh) | 食叶草活性肽的制备方法 | |
| JP5713571B2 (ja) | メイラード反応阻害剤およびＡＧＥｓ生成抑制剤 | |
| US6207702B1 (en) | Method for reducing postprandial oxidative stress using cocoa procyanidins | |
| EP2022503B1 (de) | Verkapselte Vacciniumextrakte mit ausgewogener Magen-Darm-Freisetzung | |
| EP1250852B1 (en) | Concentrate of triterpenes | |
| JP2000201650A (ja) | 育毛食品および経口育毛剤 | |
| JP4503263B2 (ja) | スフィンゴ糖脂質の製造方法 | |
| US6716465B2 (en) | Method of producing aqueous extracts from almond hulls | |
| EP1013752A1 (en) | Process for preparing food products fortified with oleanolic acid | |
| JP5122147B2 (ja) | 抗酸化作用を有する２−（２−メチルプロパノイル）フロログルシノール−１，５−ジ−Ｏ−β−Ｄ−グルコピラノシド | |
| US20070148266A1 (en) | Pine needle extract | |
| JPWO2008108001A1 (ja) | ガラクト脂質 | |
| JP5905201B2 (ja) | 食用ミカン皮およびその製造方法、ならびにこれを用いた脂質代謝改善用組成物、および飲食品の製造方法 | |
| JP2003009811A (ja) | 食品組成物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: UNILEVER PATENT HOLDINGS, NETHERLANDS Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:FRITSCHE, JAN;ROSIER, OTTO EDUARD;SCHMID, ULRIKE;AND OTHERS;REEL/FRAME:013057/0040;SIGNING DATES FROM 20020410 TO 20020411 |
|
| AS | Assignment |
Owner name: LC USA LLC, ILLINOIS Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:UNILEVER PATENT HOLDING B.V.;REEL/FRAME:014466/0202 Effective date: 20030722 |
|
| AS | Assignment |
Owner name: LODERS CROKLAAN USA LLC, ILLINOIS Free format text: CHANGE OF NAME;ASSIGNOR:LC USA LLC;REEL/FRAME:014430/0988 Effective date: 20021224 |
|
| FPAY | Fee payment |
Year of fee payment: 4 |
|
| REMI | Maintenance fee reminder mailed | ||
| LAPS | Lapse for failure to pay maintenance fees | ||
| STCH | Information on status: patent discontinuation |
Free format text: PATENT EXPIRED DUE TO NONPAYMENT OF MAINTENANCE FEES UNDER 37 CFR 1.362 |
|
| FP | Lapsed due to failure to pay maintenance fee |
Effective date: 20121130 |